dimethyl carbazole-3,4-dicarboxylate | 81787-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: dimethyl carbazole-3,4-dicarboxylate
• 英文别名: dimethyl 9H-carbazole-3,4-dicarboxylate
• CAS: 81787-91-9
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: RVXMOLXKGTZGLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl 2-vinyl-1H-indole-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 dimethyl carbazole-3,4-dicarboxylate
  参考文献：
  名称：

  The Synthetic Studies of Carbazole Alkaloids

  摘要：

  The carbazole alkaloids have profound biological activities and material properties. We reported that 3, 4-substituted, 3-substituted and 4-substituted carbazoles were regioselectively synthesized from indoline derivatives by means of Die Is-Alder reaction in the presence or absence of Pd catalyst and attained the synthesis of natural carbazole alkaloid from 3-substituted carbazole, too.

  DOI：

  10.3987/com-15-13286

文献信息

• The regioselectivity of the formation of dihydro- and tetrahydrocarbazoles by the Fischer indole synthesis
  作者：G. W. Bryan Reed、Peter T. W. Cheng、Stewart McLean

  DOI：10.1139/v82-063

  日期：1982.2.15

  The cyclohexanone 3 and the cyclohexenone 13 have been prepared, converted to their phenylhydrazones, and subjected to the Fischer indole synthesis under conditions ranging from 7% to 60% sulfuric acid in methanol. The tetrahydrocarbazoles 4 and 5 were isolated in a 2:1 ratio in the sequence starting from 3 and no significant variation in the ratio was observed through the range of conditions used. In the sequence starting with 13, the dihydrocarbazoles 14 and 15 were isolated in a 1:1 ratio when 7% or 15% sulfuric acid was used; when more concentrated acid was used, normal Fischer products were not obtained but some transformation products were isolated from the complex mixture of products obtained. The observed regioselectivity of these reactions is not predicted from mechanistic considerations, and no mechanistic explanation for the results is apparent. As part of the proof of structure of 4 and 14, their N-benzyl derivatives were prepared from 1-benzyl-2-vinylindole by Diels–Alder reactions.

  环己酮3和环己烯酮13已经制备好，转化为它们的苯基肼酮，并在甲醇中以7%至60%硫酸条件下进行费歇合成反应。从3开始的序列中，四氢吲哚4和5以2:1的比例被分离出来，并且在使用的条件范围内观察到比例没有显著变化。从13开始的序列中，当使用7%或15%硫酸时，二氢吲哚14和15以1:1的比例被分离出来；当使用更浓缩的酸时，未获得正常的费歇产物，而是从所得到的复杂混合物中分离出一些转化产物。这些反应的观察到的区域选择性并非来自机械考虑，并且对于结果的机械解释并不明显。作为4和14结构的证明的一部分，它们的N-苄基衍生物是通过Diels–Alder反应从1-苄基-2-乙烯基吲哚制备的。
• REED G. W. B.; CHENG P. T. W.; MCLEAN S., CAN. J. CHEM., 1982, 60, NO 4, 419-424
  作者：REED G. W. B.、 CHENG P. T. W.、 MCLEAN S.

  DOI：——

  日期：——
• The Synthetic Studies of Carbazole Alkaloids
  作者：Hajime Yokoyama、Yuzen Shoji、Takayoshi Kubo、Masahiro Miyazawa、Yoshiro Hirai

  DOI：10.3987/com-15-13286

  日期：——

  The carbazole alkaloids have profound biological activities and material properties. We reported that 3, 4-substituted, 3-substituted and 4-substituted carbazoles were regioselectively synthesized from indoline derivatives by means of Die Is-Alder reaction in the presence or absence of Pd catalyst and attained the synthesis of natural carbazole alkaloid from 3-substituted carbazole, too.